Cholic Acid → HCID 18652176, compound

HRID 1587014Notes

Reaction equation

HRID 1587014 reaction equation
[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:29])[C@@H:13](O)[CH2:14][C@@H:15]3[C@@:20]4([CH3:26])[CH2:21][CH2:22][C@@H:23](O)[CH2:24][C@H:19]4[CH2:18][C@@H:17](O)[C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6]>[Cl-].[Zn+2].[Cl-]>[C:5]([OH:7])(=[O:6])[CH2:4][CH2:3][C@H:2]([C@@H:8]1[C@:12]2([CH3:29])[C:11](=[C:16]3[C@H:15]([CH2:14][CH2:13]2)[C@:20]2([CH3:26])[CH:19]([CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:18][CH2:17]3)[CH2:10][CH2:9]1)[CH3:1]

Participants

3

Reactant 1

HCID 221493Cholic Acid

Product 1

HCID 18652176HCID 18652176, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Cholic acid is treated with zinc chloride to afford the corresponding chol-8(14)en-24-oic acid which is subsequently reduced by treatment with lithium aluminum hydride to the corresponding alcohol. Treatment of the alcohol with p-toluenesulfonyl chloride in the presence of 4-dimethylaminopyridine and triethylamine gives the tosylate which is then converted to the 4-chlorophenylseleno derivative by treatment with bis(4-chlorophenyl)diselenide in the presence of sodium borohydride.

Sources & evidence

ORD record
ord-e2aee0232c0544f6a1459047ace8f03a
Source dataset
uspto-grants-1993_06
Patent number
US05216015

Reaction notes

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